When You're Not Expecting
by Lint
Summary: He's that guy. Pre-series, AU.


Okay, he's that guy.

The one doesn't know how the hell got an invite to the party. The one who doesn't know why it suddenly became very important that he go. The one who's sitting on the couch all by his lonesome because no one will talk to him, reading Voltaire because he found it on the bookshelf by the bathroom.

"Well, aren't you pathetic?"

Looking up to see a pair of shrewdly judgmental eyes, dark and oddly pretty. A face like porcelain, framed by elegantly curled chestnut tresses, all perfectly coiffed and topped off with the crown of a headband. Lips full but not pouty, the words that pass through them appear to be in his native sarcasm.

He wants to ask how pathetic is he really if she, obviously one of the elite social butterflies, is talking to him. Keeping his mouth shut is a rarity, but it appears to be the right decision, when she pulls the book from his hand instead of turning and going elsewhere.

"Kind of heavy reading material for this crowd," she says, thumbing through the pages.

"Well I guess the party scene is not really mine," he replies.

She looks him up and down.

"Clearly so."

Later they're bickering back and forth as of they've known each other forever. Words he never uses amongst his regular circle, _esoteric, archaic, ill conceived dreck_, fly between them like arrows on a battlefield.

She matches every reference he makes with scathing rebuttal, those eyes and lips scowling with opinion considered vastly superior to his own, and he counters those points with a flurry of over analyzed rhetoric. Poetry in motion sparring with an immovable mindset.

Only when the party irrupts in a bevvy of catcalls, is their conversation interrupted. Looking over to see a girl, all legs and shimmering blonde locks, dancing atop a table as if she hasn't a care in the world. Dan is hypnotized for a second, because she's clearly gorgeous, and wonders if this is going to turn into a strip tease of some kind with how drunk she appears to be.

Blair is noticeably annoyed, arms folded and brow furrowed.

"I guess some people really need attention, huh?"

It must be the right thing to say, because it's the first smile he's gotten out of her the whole time they've been talking.

/\

Honestly, he never expected to see her again. Talking to a girl at a party didn't automatically make you friends, so it's genuine surprise on his face when she approaches him in the hall.

"Is this going to be a thing?" He asks when she pulls the book from his hand, once again without asking.

"Nietzsche?" She says with a roll of her eyes. "Not while the sun is out Humphrey. Also? I forbid you to paint your nails or dye your hair black because of this doom and gloom."

He rankles automatically against the command, not a fan of being ordered around, let alone so early in their... Whatever this is.

"Is that a risk?"

She grabs his wrist, smiling wickedly as she slips the book back into his hand. Goosebumps dot his skin at the contact, and he chews the inside of his cheek so as not to blurt out the first thing that pops into his head.

Pay attention now, a voice warns.

This girl is dangerous.

/\/\/\

Oh, he's that guy.

The one with a famous dad. The one with his picture taken with a dozen stars of the movie and rock variety that adorn the walls of the house. The one whose dental x-rays were used as the cover of the band's third album, and has been certified platinum three times over.

Lincoln Hawk, one of the few "seminal" bands of the 90's who managed to keep their act together. To grow with their music enough to still be relevant almost twenty years after their debut.

Blair looks at all these facts presented in front of her with detached interest. Intrigued at some of the faces he and his sister are paired with across a splash of photos, she stops at a frame that holds no visual representation of his childhood, but the text of his first published work. An article written about the summer he got to tag along on the fifteenth anniversary tour.

"How old were you when you wrote this?" She asks.

"Um, Twelve."

"Well," she says, running her finger along the glass of the frame. "Look who just got a little interesting."

The first thing she does upon catching sight of his bookshelf, is pull Cedric from his perch and hold him in the crook of her arm. Eyes scan the various titles of his collection, a sing song sound of _mhmm_ when she sees something she likes, and a flat _hmph_ coming across something she doesn't.

"Not bad Humphrey," she says keeping her head straight, fingers running along the spines and stopping noticeably at the last row.

"Congratulations," she says without a hint of sarcasm, turning to him with his copy of Anna Karenina in her hand. "On being the only other person I know to have read this."

There's something about how she says it, as if their shared interests carry a deeper meaning than mere coincidence.

Later, they're sitting on the floor with their backs against his bed, a small pile of books between them. Cedric still rests comfortably in her lap, having not put him down once since they came into the room. Though only possessing a cursory knowledge to begin with, she's not at all what he might have expected. The reputation that proceeds her is nothing close to the girl sitting next to him now.

"You do realize I can't let you take him home."

Her arms tighten around Cedric, but the look on her face is playful.

"I'm sure we could negotiate a work release of some kind," she replies.

"Is that so?"

"You'll learn soon enough Humphrey," she starts, leaning in close enough that he sees the faintest smattering of freckles across the ridge of her nose, marvel at the mischief sparking in her eyes, feel her breath on his cheek. "That people seldom say no to me."

Oh.

He has no doubt about that.

/\

When she sits next to him at lunch, it feels more like a grand statement than a friendly gesture. Complete with minions, her word not his, in tow. Including, surprisingly, table dance girl from the party.

"Uh, hi."

It comes out far more awkward that he would prefer.

"I'm Serena," the blonde says with a radiant smile, sticking out a hand for him to shake.

He obliges, looking for Blair's reaction from the corner of his eye, watching the exchange with measured interest.

"Don't worry," Serena goes on. "This isn't a hostile takeover or anything. We were just curious about the guy whose been taking up Blair's afternoons lately."

It's a funny thing to say. Only Serena and Blair even bother to acknowledge his existence. The other three girls look as bored and detached as anyone can be sharing a table with him, preferring their phones to the conversation.

Dan has never been quick with social graces. It's why it takes him a few minutes to realize it's Serena that commands this little court of theirs. It seems kind of odd, what with all of Blair's authoritative pomp, that she isn't the one reigning supreme. Serena is so bubbly and animated, talking endlessly about this and that, she doesn't even notice that no one else is participating. He wonders if this is some sort of litmus test, Blair dangling her attractive and lively friend in front of his face, and seeing how much attention is paid to her afterward.

_Hey_, Dan mouths at her.

She smiles.

_Hey._

/\/\/\

Yeah, he's that guy.

The one who punches Chuck Bass in the face within five minutes of meeting him. The one standing awkwardly out of place in a room full of the upper crust, who all regard him with disapproving glares. The one who really should have thought out physical retaliation because his hand is throbbing.

Blair is mortified. Cheeks flushing scarlet at his act, anger burning in her eyes. She grabs his arm so hard, he's sure there will be the crescent moons of her fingernails dug into his skin, even through the jacket sleeve. Only when they reach an empty hallway, far enough from the ballroom, does she lay into him.

"I realize your money is generated from the excess of sex, drugs, and rock n' roll. But I had foolishly assumed that your literary credibility would translate into a basic set of manners at the very least."

For a second he can only stand there, a thousand words of defense generating in his brain, but all fail to cross the finish line of his mouth. It's hard to fathom someone like Chuck Bass exists. No one their age dresses, acts, or talks like him. Dan knew right away he's the kind of rich kid who does whatever he wants without fear of consequence.

You don't meet someone and within seconds tear them down due to some haughty sense of superiority. You don't say things about the girl he accompanied, who's supposed to be his friend, to try and get a rise out of the new guy.

It wasn't unprovoked. He doesn't go around hitting people for no reason, let alone in a room full of witnesses. She has to know that much.

"Oh come now, Humphrey," Blair continues, folding her arms. "I think we both know silence is not your strong suit."

He wants to say so many things, but nothing forms coherent. Instead he just stands there biting his tongue and hanging his head. When Blair storms off, he doesn't give chase.

Later, he's sitting next to the kitchen with a bag of ice one of the staff was nice enough to give him, propped atop his hand. He probably should have left when Blair walked away, but a step from the exit he found himself turning back, halted by the fact that he can't stomach the idea of her hating him.

There's isn't much of a plan beyond waiting her out in the lobby once the brunch disperses, dropping to his knees and begging forgiveness.

He thinks he's seeing things when she suddenly rounds a corner and appears before him.

"Found you," she says, slowing her steps.

"How'd you know I wouldn't leave?"

"I didn't," she replies, taking a seat next to him. "Just sort of hoped."

"Look Blair, I'm so sor-"

"No apologies necessary, Humphrey."

She removes ice from his hand, examining the bruising, as her thumb rubs gently across the knuckles.

"Nate told me what Chuck said to make you go all barbarian on him."

Nate? Chuck's BFF and Mary Jane confidant? Dan never thought him a bad guy despite the company he keeps, but is a little shocked he would rat his friend out for someone he barely knows.

"Not my finest moment."

She smiles softly.

"Defending my honor gets you a pass. But just this once."

He nods compliantly. She's still holding his hand.

"Why are you friends with a guy like that anyway?"

"He's Chuck," she answers with a shrug. "He's not like that all the time. Besides, he only said what he said to get a rise out of you, and guess what? You reacted exactly how he wanted."

"And now I want to hit him again."

She actually laughs.

"What am I supposed to do with you?"

/\

Dan is on his best behavior when meeting Blair's dad.

He puts his napkin in his lap, chews with his mouth closed, and keeps his elbows off the table. All an overcompensated attempt of being a perfect gentleman. It was supposed to be both of her parents, but her mom had some kind of emergency at her design studio, so it's a small relief having to deal with only one.

Harold Waldorf is an impossibly charming man. The exuberance in which he cooks dinner, making chopping, fileting, and frying a show that could easily be televised. It doesn't take a genius to see that Blair is the apple of his eye, and despite the mild mannered appearance, Dan knows he'd been on the short end of one of the man's many knives if he ever steps out of line with her.

It's also obvious that Blair adores him, the affectionate way she still calls him daddy, how her cheeks go red when teasingly brags about her accomplishments. When she takes his hand under the table, Dan is decidedly glad that Eleanor is not here.

Mothers tend to notice things like a teenage boy falling madly for their daughter.

/\/\/\

So, he's that guy.

The one with his face plastered all over the internet. The one with his name being dragged through the grinders of the Upper East Side rumor mill. The one who had the audacity to kiss Blair Waldorf in public.

It's not as if he planned it, though the thought has been prevalent for some time, it happens because he's losing an argument. Walking out of the theater, eyes focused on the sidewalk, as Blair proceeds to use that vast vocabulary of hers to rip his intellect a new one.

For opinions expressed contrary to hers, in regards to Audrey Hepburn and the director's decision to dub over her singing in _My Fair Lady_. He for, she against. Looking up at her, eyes alight with the fierce desire to prove him wrong, he just cups her face in his hands and ends the argument with his lips.

She freezes under his touch, fear pooling in his stomach that a horrendous mistake has just been made, but then her hands curl around his wrists as she sighs against him and it feels like _finally._

Later, he's sitting on the couch flipping through the channels while Jenny remains vigilant in front of the computer, feeding him updates anytime someone new decides to comment on the post made about he and Blair's public displays of affection on that meddlesome website.

Being called a variety of odd things, ranging from comparisons to household pets and breakfast pastries, to a desperate wallflower looking for his fifteen minutes. It's definitely an adjustment to have a target on his head, leaving him to wonder if falling for the school's resident mean girl isn't the smartest thing he's ever done.

Blair send a text.

_Discovering a sudden hatred for anyone who possesses a camera phone. Enjoy the spotlight while it lasts, Humphrey. _

He smiles at the screen. Some things are worth the risk.

/\

Serena corners him in the hall, all blonde and leggy, the liberties taken with the uniform every bit the naughty schoolgirl.

"I need to give you the talk."

He swallows audibly.

"The what?"

"The 'Blair is my best friend in the world, and if you ever hurt her in any way, I will rip out your heart and show it to you' talk."

He blanches at the statement, momentarily confused. While his life has just been threatened in gruesome detail, the light and friendly way in which it was issued, leaves doubt as to true intent. The way she caps the whole exchange off with a megawatt smile and loops her arm through his, doesn't offer any clarity either.

She guides him to the quad, where Blair's face sours instantly up seeing them paired up, and all he can do if offer a helpless shrug. The insecurity surrounding their friendship would be kind of funny if Dan didn't think it so ludicrous. Blair might not be as open and outgoing as her counterpart, but commands respect in her own right, and is every bit the queen she wishes to be.

Disengaging from Serena, he takes a seat next to Blair, who's still scowling.

"Care to explain?" She asks in a harsh whisper.

"I got the talk."

"What talk?"

"The 'if I ever break your heart, she gets mine on a plate' talk."

She looks over to Serena, who cocks an eyebrow smugly. Under the table, Dan grabs Blair's hand before leaning over to kiss her, soft and sweet.

Her eyes are still closed when he pulls back, allowing himself a moment of satisfaction before, "Think I'm kind of attached to you, Waldorf."

Oh, the smile she gives him before leaning in to rest her head on his shoulder.

"I suppose I can make do."


End file.
